These CIOs hear pitches every day; here’s what makes them listen

When you’re selling technology to enterprises, the CIO’s sign-off is almost always required before you can close the deal. And where buying power concentrates, so do salespeople. In their attempts to catch the attention of an audience that’s often numb to sales pitches from hot new technology startups, many sales reps fall victim to bad sales habits that land them on the blocked caller list. To help you understand the right way to reach this coveted audience, I collected the wisdom of a dozen CIOs who are part of Lightspeed’s CIO Innovation Advisory Network and who hear sales pitches day in and day out. Which pitches make them listen, and which do they tune out?

Don’t Pitch. Have an interesting conversation instead.

The best sales pitch isn’t a sales pitch at all; it’s an interesting conversation. That means not always leading with the product — sometimes the most interesting sales conversations don’t start with the typical pain-point-product-fit dialogue.

A luminary CIO in the Entertainment industry recalls:

One sales rep I remember really researched me… and made an online donation to one of the non-profit organizations I support and am on the board of. He made the donation in my name and therefore I received the email from the organization notifying me of the donation and in it he said, ‘I know your time is valuable and I respect your time so I made this donation in hopes that I could have a 10-minute call with you.’ Of course I scheduled the call.

Although a great way to catch the attention of a busy CIO, you don’t always have to make a charitable donation to stand out. A simple, friendly approach is just as effective.

A CIO from the Pharmaceutical industry recalls:

Recently I met a mobile device management vendor at a conference. I told her I was planning on using one of their competitors so I was not interested as I already vetted out most other vendors. She said she understood, but asked if I was willing to attend a 30 minute conference call demo to get an overview of the product. She also promised no salesperson would call me. I agreed and their product turned out to be pretty compelling and not only met one need, but several. No pressure at all and they made the process easy.

When selling to CIOs, the cookie-cutter product pitch almost never works. Being genuine, polite, and understanding will get you a lot further than being pushy and demanding.

Avoid the not-so-eye-catching sales gimmicks

We all know the prototype: the auto-email send that’s designed to look like a personal touch but never quite manages to veil a sales org’s complete lack of awareness. These pitches simply don’t work. Period.

The CIO of a large financial institution in NYC adds:

Gimmicks are completely NOT appreciated (no random emails like “why haven’t you responded?”, “have you not responded because you were attacked by an alligator?”, “ l will give you an iPad to respond”, etc.). The more aggressive the salesperson, the less interested I am. I feel like I am only going to get added to all their junk mail lists and not get anything useful out of it. The most successful cold outreach was a carefully tailored message that talked to me and my specific needs. It involved the fact that the salesperson had done real research on us. I felt that the person had taken time to write the note rather than just filled out a form letter. The email needs to come from a human, not a mass mailing process.

The gimmicky sales emails and the insistent voicemails simply turn off your prospects and hurt your chances of reaching them. Time wasted trying to be clever is better spent reaching out to your network for a warm introduction or tailoring a message to a specific CIO.

The CIO of a large insurance company shared the following advice:

Not realizing that the timing or fit just isn’t there — but continuing to push as if somehow that’s going to change things — will never work. I don’t take cold calls/emails. It needs to be referred either by another CIO, a VC with which I’m familiar, or similar.

The meaningful relationship always wins

This age old advice is worth repeating. Your prospects are people, not faceless corporations. Building a relationship with a client goes beyond being friendly and genuine in your initial outreach, or up until you close a deal; it means building a long-term relationship with your prospect. To do so, you have to be continuously meaningful to them as their needs and challenges shift.

To the CIO of a semiconductor firm

the rep who was most memorable to me made me feel they cared about my problems. My problems became theirs, not something they fix and run away.

Building a long term relationship with your prospect can be as simple as scheduling a regular call. Even busy CIOs will agree to a scheduled call cadence if you can prove to them that you are committed to the relationship and that you will add value now and whenever new needs come up.

A telecom CIO echoed the same sentiments:

One of the best reps I worked with proactively connected with me to understand my priorities, opportunities, and pain points. It was not just a connection where the person was only interested in a sale to meet their quarterly quota. The person provided flexibility in the deal and didn’t hide behind ‘corporate will not approve that’. As an account manager, the person was partnering with me to offer solutions.

Don’t Get Discouraged

Timing is everything so even if you have the best thing since sliced bread, you may not get the traction you need right away. In these instances, keep building and nurturing your relationships. A highly-respected CIO from CPG industry advises:

My decision about whether or not to engage with you is based on competing demands on my time, if my company needs your product or service and it’s a priority, and if I have the budget. I may love your product but if it’s not in the budget for another two years, it’s unlikely you’ll be able to convince me to look at it now. Invest this time in getting to know the industry, my products and pain points.

Admittedly, none of the advice in this article is particularly new, but it all bears repeating as new technology and tools make it ever easier for sales reps to find and reach CIOs. Even in a world fully driven by AI and bots, the personal approach will always be the one that stands out.